The shady side of Tobey Maguire

In the last 10-or-so years, Tobey Maguire has pretty successfully flown under Hollywood's gossip radar; however, now that the Seabiscuit star is newly single, some of the shady alleged moments from his past are suddenly coming back to light. Here are the sketchiest rumors about Maguire's personal and professional lives—that we know of so far.

He was involved in a sketchy gambling ring

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Maguire reportedly loves to put his big earnings to the test by hitting up poker tables and betting tons of money on games. Unfortunately for him, not all of those games are legit. The Hollywood Reporter claims that Maguire had to dole out $80,000 after he and 22 other stars were named as participants in a series of illegal, high-stakes poker games. The games were hosted by hedge fund manager Brad Ruderman, who was convicted of running a Ponzi scheme.

Maguire allegedly won more than $300,000 in the illegal games, which a bankruptcy judge claimed was unlicensed, making the winnings "ill-gotten gains" from Ruderman's clients.

A source told Star (via Radar Online) that Maguire was a "very, very frequent player" at Ruderman's games, winning as much as $1 million a month over a three-year period. "That means he could have made up to $30 to $40 million from these games," the source alleged.

Maguire shelled out $80,000 and "represented to the best of his knowledge that he has not received any more money than those poker winnings from Ruderman," according to the Hollywood Reporter. Maguire claimed to not know anything about Ruderman's Ponzi scheme.

He allegedly was not nice to his poker partners

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Molly Bloom, the woman who allegedly organized some of the poker games at the infamous Viper Room, wrote in her book Molly's Game (via Vanity Fair) that Maguire once humiliated her when he was at the tables by demanding that she "bark like a seal who wants a fish" in order to earn a $1,000 poker chip. When Bloom allegedly attempted to laugh it off (because, well, who would think he was serious?), he reportedly persisted, telling her, "I'm not kidding. What's wrong? You're too rich now? You won't bark for a thousand dollars?"

Fortunately for everyone, she would not.

His diva demands almost cost him 'Spider-Man 2'...

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Maguire reportedly took home a cool $4 million for the first Spider-Man—which is huge in itself and especially huge compared to the relatively paltry $500,000 that Andrew Garfield allegedly pocketed for The Amazing Spider-Man. Even more impressive was the $17 million deal he reportedly earned to reprise his role two years later.

Except, getting to that point was reportedly fraught with tension. When it came time to suit up in tights again, Maguire allegedly became such a diva during pre-production that he was briefly dropped from the film and almost replaced by Jake Gyllenhaal. According to Variety, some of the issues that led to the behind-the-scenes fiasco included Maguire's complaints of having back problems, which the studio, Columbia Pictures, felt was a threat being used during negotiations. The Los Angeles Times, meanwhile, claimed that Maguire neglected to show up for body scans needed for the film's special effects, a decision Maguire later regretted.

Once Maguire got word that he was being replaced by Gyllenhaal, his team of reps, as well as his then-girlfriend's father, studio honcho Ron Meyer, "stepped in to save the day" and assured the studio that both Maguire and his back would be just fine on set, according to Variety. He even agreed to medical tests to prove his back was in tip-top shape during contract re-negotiations, according to the report.

"I'm just glad it worked out. I'm glad I got to look these people in the face and say, 'I'm really sorry. I'm going to do whatever it takes,'" Maguire later admitted to the Los Angeles Times.

And then he dumped his agent

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According to the Los Angeles Times, shortly after Maguire was reinstated as Spider-Man, he fired his agent of seven years, Leslie Siebert. This led to speculation that Siebert was fired "as a consequence of the near-debacle," according to the report. Maguire downplayed his decision, telling the Times, "It's just a business decision and she's not the scapegoat." "I did not know how to handle that parting where anyone feels good about it," he added, regarding their final meeting. "I was dreading it…It's a real bummer for both of us."

But not everyone saw it as a simple "business decision." "[Siebert] was unfairly singled out. I promise you she wasn't the one who should've taken the hit," an insider told the Times. Siebert herself seemed unhappy about the fallout, telling the New York Daily News, "It's an unfortunate end to a very successful seven-year relationship." Ouch.

He was allegedly mean to Charlize Theron

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According to sources for the Los Angeles Times, Maguire was so cruel to Charlize Theron on the set of The Cider House Rules that the film's studio, Miramax, stepped in and "[told him to] cool it."

Theron—who has been honest about her feuds with co-stars before—seemingly confirmed the reports in a 2016 interview with V magazine (via Entertainment Weekly). "Tobey and I had a bit of a rough time … It was a difficult movie," she said. "Every day is completely different for a completely different reason. Whether it's the weather, or the writing isn't there, or you don't get along with your castmate, you have to be able to go to something else that's just as powerful."

"Does it make it as enjoyable? Probably not," she added. "I mean, there were just a couple of days that Tobey and I had a rough time." Sounds like a blast.

He didn't get along with James Franco, either

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Add James Franco to the list of stars who didn't always get along with Tobey Maguire on set. In an interview with Playboy (via Starpulse), Franco—who appeared in Spider-Man and Spider-Man 2—confessed to director Sam Raimi that he became jealous of Raimi's working relationship with Maguire, as well as Maguire's budding relationship with co-star Kirsten Dunst. "I felt you gave Tobey Maguire so much attention during Spider-Man…that I didn't get as much of your love as he did," Franco said. "Tobey and Kirsten became a couple around that time. I had a crush on Kirsten, and I think I was upset about that as well."

"Tobey was mad at me for a while," Franco added. "By the second film, we were cool, but that's another reason I felt hurt, with you giving Tobey all the attention…You were the father who wouldn't give me the love I needed." Awww.

He may have a hot temper

In July 2008, Maguire flipped out at a group of photographers outside a West Hollywood eatery for having the nerve to try taking his picture. To be fair, paparazzi generally don't seem like a fun bunch of people to deal with, and driving with flashing lights in your face isn't easy or safe for anyone; however, the restaurant at which Maguire and Meyer were dining, Madeo, is said to be a hot zone for paparazzi and their celebrity victims. In any case, here's hoping he sticks to more low-key restaurants.

He was a member of Leonardo DiCaprio's, uh, posse

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Back in the '90s, Maguire was a member of Leonardo DiCaprio's infamous "P***y Posse," which was the subject of a somewhat damning profile published by New York magazine in 1998. Somewhere along the way, Maguire and DiCaprio agreed to star in an independent, improvisational movie called Dom's Plum, about a group of young Los Angelenos who meet at a diner to "compare notes on masturbation, harangue fellow customers and generally behave like young people do in movies they write themselves," according to the Guardian.

Perhaps unsurprisingly, Maguire allegedly has since fought tooth and nail to prevent it from seeing the light of day. Things got so bad that, in 1998, producer David Stutman sued Maguire and DiCaprio, alleging that Maguire used DiCaprio's influence to get the film banned, in part because Maguire was concerned that his "improvisational comments [would] undermine his public image," according to Vulture.

In the settlement, it was agreed that the film would not be released in the United States or Canada. Another producer tried to stream the movie online for free in 2016; however, that attempt was quickly squashed. Shady, indeed.

He moved on very quickly after his split from his wife

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As Nicki Swift previously reported, Maguire split from his wife, Jennifer Meyer, in October 2016 and almost a decade of marriage. Just one day after the couple announced their separation, it was revealed that Maguire, a 41-year-old father of two, has been hitting the club scene again with "P***y Posse" leader DiCaprio—and has been going at it for months.

In fact, TMZ reports that Maguire approached the barely-legal Sofia Richie at a nightclub. In fact, he allegedly got very close to Justin Bieber's 18-year-old ex, but she wasn't interested.

To be fair: sources for Page Six claim that Meyer knew about Maguire's clubbing and that she's been going out, too. But, still: come on, dude.